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From towering skyscrapers to inspiring culture, Chicago is a city that calls to travelers from near and far and offers endless history and adventure. With so much to see, experience, and do, it’s a place that promises to satisfy visitors with all types of interests and agendas in mind.

Whether you’re here solo to see the art or can’t wait to spend time with the entire family in tow, there are plenty of options for fun to choose from. The following are 15 to consider adding to your must-do list the next time you’re in town.

15. Mob & Crime Bus Tour

a mural of mobster john dillinger on the mob bus tour

(image via Chicago Crime Tours)

It’s no secret that Chicago has a past steeped in some shady business. If you’re a visitor interested in learning more about those mob bosses that once ruled the streets of the Windy City, a mob and crime bus tour might be for you!

These 90-minute tours introduce passengers to big names of the prohibition-era mobs, including Bugs Moran, Al Capone, John Dillinger, and Dion Johnny Torrio. Local historians will show you those places and spaces where mob bosses once wreaked havoc.

14. Dig Into Some Deep Dish Pizza

a deep dish pizza at burt's place in chicago

(image via Burt's Place)

Deep dish pizza is the final form of pizza in Chicago. This trendy city takes on New York’s challenge for the finest pizza on the planet. With locally sourced ingredients and world-class chefs, the thick savory crusts are difficult to surpass. From hole-in-the-wall joints to upscale establishments, you’re guaranteed to find your favorite pizza taste here. Burt’s Place is Chicago’s leading Pan Pizza restaurant. Whether you dine in or take away, their carmalized crusts are guaranteed to please when you visit Chi-Town.

13. Garfield Park Conservatory

flower arrangements at the garfield park conservatory

When the city’s hustle and bustle has you craving some quiet time in nature, you don’t have to go far to find it. Time at the Garfield Park Conservatory gives visitors a chance to immerse themselves in natural beauty within the parameters of an impressive botanical space featuring no less than eight indoor gardens.

Since its construction in 1908, Garfield Park Conservatory has provided visitors with a place to relax, admire nature, and find some much-deserved peace of mind. There’s something for every outdoor enthusiast here, from waterfalls and palm gardens to on-site yoga and gardening demonstrations.

12. Shop the Magnificient Mile

the start of the magnificent mile at the chicago river

If you’re the type of traveler that’s looking forward to shopping their way through a city stay, then time on the Magnificent Mile is an absolute must. Covering eight city blocks of Michigan Avenue, the Magnificent Mile is a space adorned with incredible architecture, delicious dining options, and of course, endless shopping stops to check out.

More than 460 retailers call this area home, including boutiques and flagship stores. With more than 275 restaurants nearby, there’s no shortage of flavor and fun waiting for you.

11. Museum of Science and Industry

the exterior of the museum of science and industry

If you’re in Chicago with little ones, make sure to check out the Museum of Science and Industry. This event pairs education with engagement and fun that will keep your kiddos hooked.

From the full-size German U-505 submarine on-site to the stainless steel diesel locomotive dating back to 1934, visitors will find there’s much to explore and a lot of inspiration to be gained in the process. Exhibits here cover everything from how storms form to the Apollo Missions that have made their way out of this world over the decades.

10. Architecture Boat Tour

tall skyscrapers in chicago along the chicago river viewed from a boat

Experience the iconic architecture of the city from the greatest seat in the house—the river. Their knowledgeable tour guides explain the skyline’s 130-year history, while bartenders and staff keep you comfortable and entertained. This thorough trip follows all three branches of the Chicago River into the city’s center. It’s the one thing everyone urges you to do in Chicago, and it has to be done perfectly.

9. The Richard H. Driehaus Museum

the main hall and staircase of the richard h driehaus museum

If history gets your heart racing, touring the Richard H. Driehaus Museum will be a delight. This 1883 home is an icon of the Gilded Age right in the heart of Chicago’s Magnificent Mile.

Originally constructed for banker Samuel M. Nickerson, this home and museum is a great place to step back in time and enjoy an immersive tour experience complete with era-specific furnishings and art nouveau elements. Make sure to swing by the home’s ballroom before you go, which also doubles as an art gallery in its own right.

8. Attend a Cubs Home Game

the historic marquee on wrigley field

(image via Chicago Cubs)

If you’re a baseball fan, a trip to Chicago should always include some well-earned time at the infamous Wrigley Field. Home of the Chicago Cubs, this is considered the second-oldest baseball park within the entire MLB.

From its ivy-covered outfield walls to the manual scoreboard that demands respect amongst baseball fans of ALL teams (you, too, Cardinals), time at Wrigley Field is equal parts thrilling and nostalgic. Whether you’re touring in the off-season or heading in for a game, it’s a moment you won’t want to miss.

7. Millennium Park & Cloud Gate

a view of the cloud gate sculpture also known as the bean in millennium park in chicago

(image via Millennium Park)

Another structural icon of the city (found much closer to the ground) is Cloud Gate. When you’re looking for that quintessential Chicago photo opportunity, this is the place to be.

Cloud Gate is a sculpture created by Anish Kapoor, first installed in 2006 as a part of the AT&T Plaza in Millennium Park. Often referred to as The Bean, this sculpture is a sparkling silver arch made of reflective stainless steel plates. The reflective quality is sure to captivate the imagination and set the scene for some incredible photos.

6. John Hancock Center

a view looking up the john hancock center building from street level

(image via John Hancock Center)

For those in Chicago with a passion for architecture firmly intact, taking time to admire the John Hancock Center is a must. This 100-floor masterpiece is found at 875 North Michigan Avenue and towers 1,499-feet into the sky ground to tip.

The John Hancock Center has long been a defining element of the Chicago skyline. Visitors can head up to the 94th floor, where there’s a café, bar, and plenty of interactive displays to enjoy. Oh, did we forget to mention the stunning panoramic views?

5. Navy Pier

an aerial view of navy pier in chicago jutting out into lake michigan

(image via Navy Pier)

No trip to Chicago is truly complete without a stop at Navy Pier. This prime tourist attraction extends out over Lake Michigan and includes access points to rides, attractions, restaurants, movies, and more.

It’s a family-fun stop that hosts weekly fireworks in the summer (you’ll want to be sure to check those out). It’s also the place visitors can enjoy the Chicago Shakespeare Theater!

4. Stroll the Riverwalk

public park steps along the chicago river and riverwalk

(image via Chicago Riverwalk)

If you’re looking for a scenic route that takes you past some of the most iconic stops in the city, a stroll along the Riverwalk is for you. This 1.25-mile path cuts straight through downtown, taking you past places like the Wrigley Building and many public art stops.

From the Riverwalk, it’s easy to hop aboard a water taxi or even rent a kayak if you’re feeling up to some on-the-water fun. It’s a beautiful mix of urban excitement and natural beauty you shouldn’t miss.

3. Grant Park & Buckingham Fountain

buckingham fountain lit up at night

For the outdoor-minded, an afternoon spent at Grant Park could be the highlight of your stay. Situated on the Lake Michigan Loop, this is one of the city’s most iconic green spaces to enjoy covering more than 319 acres.

Come here to unwind and people watch or swing by during one of the city’s many vibrant festivals. Grant Park also hosts a collection of tennis courts, baseball diamonds, and walking paths to enjoy.

2. The Art Institute of Chicago

a walking bridge from millennium park alongside the new wing of the art institute chicago

If you’re the type of traveler headed to Chicago for art, spend some time at the Art Institute of Chicago. Some consider this one of the best museums. Visitors can admire works by Edward Hopper, Grant Wood, and Seurat alike when they drop by.

From Impressionists like Monet to modern marvels like Jackson Pollock and Warhol, this stop has it all. Before you go, don’t forget to enjoy exhibits showcasing Roman artifacts, Egyptian pottery, jewelry, coins, and more.

1. Willis Tower Skydeck

a view from the willis tower observation deck looking down toward the ground through a glass floor

(image via Skydeck Chicago)

For more than 25 years, the Willis Tower held the title of the world’s tallest building. Today, it still ranks in the top 25, making it the perfect place for those seeking adrenaline-pumping fun to come and get their fill on the Skydeck.

Located on the 103rd floor, this observation level offers up unsurpassed panoramic views of the city below. Enjoy a bird’s eye perspective that extends 50 miles from this vantage point.

The Skydeck is basically a glass box that allows guests to step out over the drop-off. It’s definitely not a stop for the faint of heart. You can book your ticket here. 


As you can see, Chicago has a lot to offer everyone. If you are looking for more things to do in the surrounding area, check out other weekend trips from nearby Chicago.

These areas are perfect for a quick day trip or a long weekend getaway. Explore our favorite things to do or peruse some pre-built itineraries.

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Jennifer Freehill

Howdy! I'm a vet and UniDeb graduate who's a passionate reader, writer, and data nerd. I tend to take life with a grain of salt, a lime, and a shot of tequila.